N-methyl-O-(N'-benzylacetamide)-N-(2-acetamido-2-deoxy-β-D-glucopyranosyl)hydroxylamine | 1138424-23-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-methyl-O-(N'-benzylacetamide)-N-(2-acetamido-2-deoxy-β-D-glucopyranosyl)hydroxylamine
• 英文别名: 2-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-methylamino]oxy-N-benzylacetamide
• CAS: 1138424-23-3
• 化学式: C₁₈H₂₇N₃O₇
• 分子量: 397.428
• InChiKey: ADVXHXCPXJEASC-JVNHZCFISA-N

物化性质

• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  141
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-乙酰氨基葡萄糖 、 在 deuterated sodium acetate 作用下， 以 氘代二甲亚砜 、 water-d2 为溶剂， 反应 72.0h， 生成 N-methyl-O-(N'-benzylacetamide)-N-(2-acetamido-2-deoxy-β-D-glucopyranosyl)hydroxylamine
  参考文献：
  名称：

  Stability studies of hydrazide and hydroxylamine-based glycoconjugates in aqueous solution

  摘要：

  Glycoconjugates can be readily formed by the condensation of a free-reducing terminus and a strong alpha-effect nucleophile, such as a hydrazide or a hydroxylamine. Further characterization of a series of glycoconjugates formed from xylose, glucose and N-acetylglucosamine, and either p-toluenesulfonyl hydrazide or an N-methylhydroxylamine, was carried out to gain insight into the optimal conditions for the formation of these useful conjugates, and their stability. Their apparent association constants (974 M-1) at pH 4.5; as well, as rate constants for hydrolysis, at pH 4.0, 5.0 and 6.0 (37 degrees C), were determined. The half-lives of the conjugates varied between 3 h and 300 days, All the compounds were increasingly stable as the pH approached neutrality. Conjugate hydrolysis rates mirrored those found for O-glycoside hydrolysis where conjugates formed from electron-rich monosaccharides hydrolyzed more rapidly. (C) 2008 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.carres.2008.11.007

文献信息

• Stability studies of hydrazide and hydroxylamine-based glycoconjugates in aqueous solution
  作者：Anna V. Gudmundsdottir、Caroline E. Paul、Mark Nitz

  DOI：10.1016/j.carres.2008.11.007

  日期：2009.2

  Glycoconjugates can be readily formed by the condensation of a free-reducing terminus and a strong alpha-effect nucleophile, such as a hydrazide or a hydroxylamine. Further characterization of a series of glycoconjugates formed from xylose, glucose and N-acetylglucosamine, and either p-toluenesulfonyl hydrazide or an N-methylhydroxylamine, was carried out to gain insight into the optimal conditions for the formation of these useful conjugates, and their stability. Their apparent association constants (974 M-1) at pH 4.5; as well, as rate constants for hydrolysis, at pH 4.0, 5.0 and 6.0 (37 degrees C), were determined. The half-lives of the conjugates varied between 3 h and 300 days, All the compounds were increasingly stable as the pH approached neutrality. Conjugate hydrolysis rates mirrored those found for O-glycoside hydrolysis where conjugates formed from electron-rich monosaccharides hydrolyzed more rapidly. (C) 2008 Elsevier Ltd. All rights reserved